Islamorada Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Islamorada showing a beach bar

Matecumbe

6 out of top 10 points of interest in this area

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Anne's Beach are top sights worth seeing.

Find hotels in Matecumbe

Top hotels in Islamorada

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 3.223.800 ₫ per night from 28 Aug to 29 Aug
3.223.800 ₫
5.106.487 ₫ total
28 Aug - 29 Aug
includes taxes & fees
9/10 Wonderful! (1,498 reviews)
"All good unless the beach"

Reviewed on 23 Aug 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 4.182.654 ₫ per night from 28 Aug to 29 Aug
4.182.654 ₫
6.481.140 ₫ total
28 Aug - 29 Aug
includes taxes & fees
9/10 Wonderful! (1,156 reviews)
"Excellent place for a restful weekend"

Reviewed on 23 Aug 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 4.421.381 ₫ per night from 1 Sept to 2 Sept
4.421.381 ₫
6.720.245 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,237 reviews)
"Not the best hotel in the Florida Keys, but it’s OK for cooling off for a couple of days. For me the pool by the ocean and the tiki bar were the stars of the show. Rooms were meh"

Reviewed on 22 Aug 2025

Amara Cay Resort
See all 2,178 properties in Islamorada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Anne's Beach

Anne's Beach

4.5/5(3 reviews)

If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.

Anne's Beach
Founders Park showing modern architecture, a garden and theatre scenes

Founders Park

3.5/5(2 reviews)

Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.

Founders Park
Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.

Frequently asked questions

How much does an Islamorada holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Islamorada costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Islamorada?
You can generally find lower prices and greater availability in September, October and November. Browse our cheap Islamorada holiday packages and you could get some great off-season discounts.
How many days is enough for Islamorada?
We'd recommend booking an Islamorada holiday for at least 3 days. This will give you enough time to visit top attractions such as Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, and explore neighbourhoods like Matecumbe and Plantation Key. You could even slot in one or two day trips from Islamorada.
Is it worth booking a holiday package to Islamorada?
Islamorada has all the ingredients you need for a fantastic getaway — walking trails, views and family-friendly attractions are just the start. Whether you'd like to check out attractions such as Theatre of the Sea and Hurricane Monument, or take the path less traveled, there's plenty to see and do on your Islamorada holiday.
How to find the best Islamorada package deals?
Use Expedia's filter tool to help you find some tempting Islamorada package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Islamorada package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book an Islamorada holiday as a package?
You can enjoy significant savings on your Islamorada escape by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Islamorada?
If you're considering a spur-of-the-moment Islamorada getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Islamorada?

  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Islamorada.
  2. Set your budget: Factor in expenses like food, flights and transportation when working out how much to save for your trip to Islamorada. Then, select a hotel that works with your budget, whether that's a low-cost option or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend exploring Islamorada. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right Islamorada holiday package for you.